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Issue 63, 2014
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Efficient synthesis of carbazolespirooxindole skeletons via asymmetric Diels–Alder reaction of 3-vinylindoles and methyleneindolinones

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Abstract

A highly efficient catalytic asymmetric Diels–Alder reaction between 3-vinylindoles and methyleneindolinones has been achieved using chiral N,N′-dioxide–Ni(II) complexes as the catalysts. A wide variety of substrates were readily tolerated, generating exclusively the corresponding exo-carbazolespirooxindole derivatives in excellent yields with high enantiomeric excesses (up to 98% yield, >99 : 1 d.r., and 98% ee) under mild reaction conditions.

Graphical abstract: Efficient synthesis of carbazolespirooxindole skeletons via asymmetric Diels–Alder reaction of 3-vinylindoles and methyleneindolinones

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Publication details

The article was received on 28 Apr 2014, accepted on 13 Jun 2014 and first published on 26 Jun 2014


Article type: Communication
DOI: 10.1039/C4CC03135K
Citation: Chem. Commun., 2014,50, 8794-8796
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    Efficient synthesis of carbazolespirooxindole skeletons via asymmetric Diels–Alder reaction of 3-vinylindoles and methyleneindolinones

    H. Zheng, P. He, Y. Liu, Y. Zhang, X. Liu, L. Lin and X. Feng, Chem. Commun., 2014, 50, 8794
    DOI: 10.1039/C4CC03135K

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